


Worth the Wait

by sisforsterek



Category: Teen Wolf (TV)
Genre: Bottom Stiles, Canon through 3A, First Time, Hotel Sex, Knotting, M/M, Mates, Rimming, Top Derek, Virgin Stiles, bareback, dating app, top derek/bottom stiles
Language: English
Status: Completed
Published: 2020-06-18
Updated: 2020-06-18
Packaged: 2021-03-04 01:20:49
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 3,187
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/24795325
Author URL: https://archiveofourown.org/users/sisforsterek/pseuds/sisforsterek
Summary: Stiles sees Derek on Grindr and swipes right for him.
Relationships: Derek Hale/Stiles Stilinski
Comments: 13
Kudos: 556





	Worth the Wait

**Author's Note:**

> Thanks to [thisnewjoe](/users/thisnewjoe) for the beta! You were so helpful!
> 
> Thanks to [KhaSterek](/users/KhaSterek) for the pre-read and being my muse!

One thing Stiles is excited about after turning 18 is that he can now use Grindr. So far, he hasn’t matched with anyone, except for one guy who told him that he would want Stiles to wet his pants in public to get him aroused, and Stiles is just not into that kink… but it’s only the first day. He’s been browsing for a while, trying to find someone to fit his type… tall, dark hair, eyes the color that he can’t really pinpoint, scruff, muscles.

Stiles stops when he gets to the next profile, jaw dropping in surprise. That’s Derek Hale. Derek Hale is interested in men. Maybe Stiles actually has a chance with the guy he’s been secretly in love with for the last year. He swipes right before he can think about the consequences. And then he waits. And waits. And waits.

He starts up Netflix to distract himself, because he can’t even focus on the next guy who pops up, too anxious about swiping right for Derek Hale.

Stiles is halfway through the first episode of some seriously shitty werewolf show when he gets a notification sound on his phone. He quickly checks it, not even bothering to pause the show, and curses, because it’s a message from Derek. 

**What the fuck Stiles?**

That’s it. That’s all it says.

_ The fuck? I didn’t know you liked guys.  _ Stiles sends back.

**I haven’t exactly had luck with women.**

**You shouldn’t be on here. Random hookups are not safe.**

_ You’re on here. _

**I’m a werewolf.**

_ Right, and I’m not, so I can’t defend myself. Just another reason Stiles can’t have fun. _

**Stop being an idiot. Can’t you find someone you know to hookup with?**

_ Don’t you think I’ve tried that? I’ve even been to Jungle. Only creepy guys want to get all up on this. _

_ I’d love for someone I know and trust to actually want to have sex with me, but no one is offering, so… _

**Why did you swipe on me?**

_ Don’t make me say it. Have you seen yourself? I’d have to be blind not to be attracted to you. And even if I was blind, I am a bit fond of you now that I know you. _

_ And I already know you’re a werewolf and would never hurt you, so you don’t have to worry about holding back with me.  _

_ I can’t believe I just admitted all that. _

**So if I was offering, you’d want to have sex with me?**

_ Are you offering? _

**I’d rather it be me than some random stranger.**

_ Gee, that’s sweet of you. _

**Stiles. Are you interested or not?**

_ Fuck yeah! So are you free now? _

**Meet me at the hotel on 5th street in an hour.**

_ A hotel, really? _

**Do you want the whole pack to know we had sex when they walk into the loft?**

_ Fair point. Ok. See you in an hour. _

Holy shit. Stiles is going to lose his virginity to Derek Hale. He better get his ass in the shower and get squeaky clean, because werewolf noses and all that.

—

Stiles is freaking out. He’s in his Jeep, waiting for Derek to pull into the hotel lot, realizing what a bad idea this is. Anyone who drives by will see the Jeep and wonder what it’s doing in a hotel parking lot. He’s trying to figure out if he should park on the next street and walk over when someone raps on his window. He jumps and looks over to find that it’s Derek, and he’s giving him an impatient look.

Stiles opens the door and exits the Jeep. 

“Do you think I should park somewhere else?” Stiles asks.

“Why?” Derek replies.

“If someone sees my Jeep, they’ll wonder why I’m parked at a hotel,” Stiles answers.

“Why would anyone drive down Fifth Street? There’s nothing here other than the hotel,” Derek says.

“Okay. Well, let’s do this then,” Stiles says as he locks the Jeep and shuts the door. 

“I got us a room already,” Derek tells him.

“How much do I owe you?” Stiles asks as he quickly pulls out his wallet.

“Don’t worry about it,” Derek replies.

“But—” Stiles says, but Derek interrupts with, “I said don’t worry about it.”

When Stiles follows Derek into the room, he’s surprised by how clean it is. He locks the door behind them, and when he turns around to face the room, Derek is already getting undressed. 

“Oh,” Stiles says, surprised. He pulls off his flannel as he walks over to the king-sized bed. He kicks off his shoes as he pulls his graphic tee over his head. When he can see again, Derek is already down to his black boxer briefs and sitting on the bed.

Stiles unbuttons his jeans and then remembers he has supplies in his pocket. He pulls out a packet of lube and a couple condoms from his pocket and tosses them on the bed. Then he slides off his skinny jeans, falling forward as he steps out of them awkwardly and bracing himself with his arms on the end of the bed. He takes his socks off as well and then looks up at Derek. He can’t read the expression on the werewolf’s face, and he wonders if he’s even remotely physically pleasing. 

“Now what?” Stiles asks awkwardly.

“What do you want to do?” Derek asks, and it’s softer than Stiles expected. 

“Everything?” Stiles answers.

Derek raises an eyebrow.

“What do you want to do first?” the werewolf asks.

“Make out? That’s a good place to start, right?” Stiles asks nervously.

Derek motions for Stiles to get on the bed, and once he’s halfway up the bed to him, the werewolf pulls him onto his lap so that Stiles is straddling Derek.

“Yeah, this is good,” Stiles says as he rests his hands on Derek’s shoulders, and what nice shoulders they are, he thinks.

Stiles slowly leans forward and presses his lips to Derek’s. He’s kissed before, but he still doesn’t have much experience with it. And he’s never kissed a guy before. Derek’s scruff is already poking into his skin, but it’s not unpleasant, just something he definitely notices. He pauses, waiting to see what Derek will do, but he relaxes when the werewolf puts his hands on Stiles’ hips and squeezes as he begins to kiss back. Stiles slides his tongue between his lips and licks along the seam of Derek’s lips. The werewolf opens up to him easily and soon the kiss deepens. Stiles involuntarily moans and slides his hands down to rub across Derek’s pecs. He’s already starting to get hard and he self-consciously tries to pull away, but Derek squeezes his hips a bit harder and pulls him forward so that his groin comes into contact with the werewolf’s. Stiles isn’t the only one getting hard.

When Stiles pulls away from the kiss to catch his breath, he rests his forehead against Derek’s. The werewolf rubs up his sides and back down before sliding his fingertips into the back of Stiles boxer briefs. Stiles involuntarily moves his hips closer to Derek and lets out a breathy moan. The next thing he knows, he’s on his back and Derek is above him, kissing and sucking on his neck as he yanks Stiles’ underwear off. 

“Oh, god,” Stiles says and grabs onto Derek’s back. 

“You know my name is Derek,” the werewolf says smugly.

“Oh, shut it,” Stiles says as he smacks Derek’s ass.

“Kinky. I like it,” Derek replies before sucking in one of Stiles’ nipples. 

Stiles has never really messed with his nipples before. It just never seemed like a pleasure spot, but when Derek sucks on his nipple, he feels a twinge in his groin. It’s nice, but Stiles wants Derek to focus lower, so he wraps one leg around Derek’s hip and grinds up. Derek’s hand moves to slide along Stiles’ thigh and he grinds down once before pulling away. The werewolf continues sucking, licking, and kissing down Stiles’ body until he stops at the trail of hair that leads to his dick. Derek stops using his mouth and takes in a deep breath before he groans. 

“What? I showered!” Stiles says, suddenly worried.

Derek smells him again, deeply. “You smell good, really good,” the werewolf admits.

“Oh.”

Then Derek grabs his dick and puts the head into his mouth. Stiles can’t help but thrust up.

“Sorry! Sorry!” Stiles immediately apologizes. 

Derek’s only reply is to move his finger over Stiles’ hole and massage around it.

Stiles’ hole automatically clenches from pleasure and he moves his hands to Derek’s hair. He has the strong urge to pull, so he does. Derek groans and Stiles is afraid this is all going to be over before they really get going.

“If you keep doing that, I’m going to come,” Stiles whines.

Derek pulls off of his dick with a pop. “So come.” 

“But—“

“You’re still a teenager. Your refractory period isn’t that long, is it?” Derek asks with a raised eyebrow.

“Well, no, but—“

“Then come if you have to. This is going to take a while to get you ready, anyway,” Derek explains before he goes back to sucking Stiles’ dick.

“Oh shit,” Stiles says as Derek goes back to massaging his asshole. 

Stiles is about to warn Derek that he’s going to come when the werewolf pulls off his dick and manhandles him until his knees are bent and pushed up toward his chest. Then Derek spreads his cheeks and the next thing he knows, the werewolf licks across his asshole. Stiles’ eyes roll back in his head and he lets out a stream of curse words. Derek continues licking his asshole, and then he uses the tip of his tongue in a way that makes Stiles think that he’s trying to get his tongue inside of him, and then with a little prodding, he does. Stiles had no idea that could feel so good. Derek continues to eat him out for what feels like forever. His tongue is doing amazingly sexy things to Stiles, and his stubble is scraping across his cheeks in a way that he didn’t know could feel this good. He’s back to feeling like he’s going to shoot his load, but then Derek is pulling away.

“Why’d you stop?” Stiles complains.

Derek chuckles. “Hand me the lube.”

Stiles looks around and finds it. He slaps it into Derek’s outstretched hand. The werewolf tears open the pack with his teeth and squeezes a bit out onto his finger. Then he pushes his finger straight into Stiles’ asshole with very little resistance. He pulls his finger out, gets more lube and does it again, as if he’s stuffing him full of lube. It’s wet—more so than the saliva—and a little weird, but Stiles figures that Derek knows what he’s doing. Soon one finger becomes two, which stretches for a bit and burns a little, and then the pain goes away. Then another finger, and finally a fourth finger and Stiles is wondering how big Derek is. Yeah, he’s imagined the werewolf has a huge dick before, but he still hasn’t actually seen it yet, though it felt quite large when they were grinding together just a few moments ago. 

Finally, Derek pulls away and sits up on his knees. He starts to pull his boxer briefs off and Stiles squirms sideways a bit to try to get a peek at the werewolf’s dick, and what he does see is huge and uncircumcised. Stiles swallows, his eyes widen, and he wonders how that is going to fit up his ass.

“Condom?” Stiles asks nervously.

“Not unless you want one. I can’t give you anything,” Derek replies. 

“Okay then, bareback it is,” Stiles says.

Then Derek is spreading his cheeks again and Stiles feels the head of Derek’s cock at his asshole. The werewolf moves Stiles legs so that they drape over his shoulders, which is slightly more comfortable than having them bent against his own chest.

Derek starts to push in and it’s definitely bigger than the four fingers he prepped him with, so Stiles takes the advice of all of the sex blogs he’s read and bears down. Soon the head slips inside and the rest of the slide in is still slow, but slightly less painful. The pain isn’t as bad as he was imagining moments ago. He thinks he can handle this. Derek slowly pulls out most of the way and squirts more lube onto his cock before slowly pushing back in. It’s becoming less painful with each glide, and Stiles shifts slightly, trying to find a position where Derek’s dick finds his prostate. 

“I’ve heard it’s more comfortable if I’m on my hands and knees,” Stiles says suddenly.

Derek frowns. “I want to see your face, but if you want, we can switch.”

“That was almost romantic, Derek. Okay, I kinda like seeing your face too. Let’s stay like this,” Stiles replies, trying his best to hide his grin at Derek’s answer.

After a few more strokes in and out, Derek starts to pick up the pace. It does feel good, but not amazing, so Stiles squirms again. Taking the hint, Derek shifts Stiles so that his hips are a little higher and on the next slide in, Stiles screams in pleasure. “Fucking yes, do that again, harder!”

Derek chuckles and picks up the pace. Instead of pulling out, he grinds in place a moment and Stiles squeaks in a totally unmanly way, but he doesn’t care, because Derek is hitting his pleasure spot and it feels fucking amazing.

On the next push in, it’s slightly painful again, but he doesn’t think anything of it, until the next slide in is painful too, and the one after that.

“Uh, Derek. What’s happening? I feel like you’re stretching me again,” Stiles says a bit worriedly. 

“Oh shit,” Derek replies as he pushes in again. 

It’s still painful, and then when Derek tries to pull out, it’s as if they’re stuck. Stiles eyes widen. “Did you just fucking knot me, Derek?”

Stiles looks at Derek awaiting an answer, but Derek won’t meet his gaze.

“Derek?”

“I… yes?” Derek finally answers.

“Why didn’t you warn me? It seems inappropriate to knot someone during sex without first telling them that’s even possible, because I thought this was just a myth, like in fan fiction. Derek?” Stiles is rambling now. If they’re going to be stuck in this position for who knows how long, things are going to get awkward fast. And why isn’t Derek replying? “Say something!”

“It’s… it’s never happened to me before!” Derek yells back.

“Oh.” Stiles said. And then after a beat. “So why did it happen now?” 

“I don’t know,” Derek says softly.

“Alright, well… don’t stop. I guess you can’t pull out, but— it felt good when you just, like, ground in place before? It massaged my prostate and I think I can still get off on your dick if you do that again,” Stiles is rambling. Again, he knows, but he’s not sure what is normal in this situation.

“Ok,” Derek says quietly, and then starts moving again.

Stiles pushes against Derek the best he can, moaning when the angle is just right and the head of the werewolf’s cock rubs against his prostate. He feels so amazingly full, and when he feels like he’s getting close again, he grabs his dick and starts to stroke it. “Fuck, yes, keep doing that. Fuck, fuck, fuck, Derek!” Stiles shoots all over his hand and chest. His ass is clenching and Derek is groaning. Suddenly Stiles feels a splash inside him, and he realizes that Derek is coming too. It’s like every time his ass clenches, he feels a new splash of cum inside him. 

“So I guess you don’t know how long we’re stuck together?” Stiles asks after he’s had a chance to catch his breath. 

“No,” Derek groans. He’s grinding his hips and still coming, and Stiles is secretly pleased that Derek seems to be having the longest orgasm ever, with him.

“Okay, well, it’s just that this isn’t the most comfortable position,” Stiles complains.

Derek pauses for a second and lets Stiles legs fall to his hips before he leans forward and scoops Stiles up into his arms, both of them moaning at the feeling when the knot tugs against Stiles’ rim. When they’re face to face, Stiles kisses Derek with a lot of tongue through his now permanent smile, and Derek kisses back for a moment before he arranges them with Derek on his back and Stiles on top straddling him. 

“Is this better?” Derek asks.

“Much better,” Stiles says as he stretches his back. 

Derek has finally stopped grinding against him, but Stiles can feel that his knot is still swollen. The werewolf is slowly rubbing up and down Stiles back with one hand, the other hand is massaging one of Stiles’ asscheeks. 

“Thanks,” Stiles says.

“For what?” Derek asks.

“For taking my virginity,” Stiles answers. “I’m glad it was you. You always take care of me when it matters.”

Stiles is worried that he’s said too much when Derek doesn’t say anything.

“Derek?”

“I lied,” Derek says suddenly.

“About what?” Stiles 

“I know why I knotted you. I didn’t know it would happen, but I know why it happened,” Derek answers.

“Is it because I know you’re a werewolf, so you could let go with me?” Stiles asks.

“No,” Derek says.

“Oh. Then why?” Stiles asks.

“You’re important to me,” Derek says.

“Oh,” Stiles says sadly.

“Are you disappointed that I told you that you’re important to me?” Derek asked angrily.

“I just thought it would be more than that. I mean, you’re important to me, too, but… I feel more for you than you do for me apparently,” Stiles says as he tries to pull away, but he can’t, because they’re still stuck together.

“Stiles. Ow, wait,” Derek says and he grabs onto Stiles’ hips.

Stiles is frustrated that he can’t pull off of Derek, and sore because the knot is even bigger than Derek’s already huge cock. “What, Derek? I have strong feelings for you. I’ve done what I always do and fell in love with someone who only sees me as a friend,” Stiles says, crossing his arms and refusing to look at Derek.

“You love me?” Derek asks.

“I just said I did,” Stiles replies angrily.

“Stiles, I love you too. I just thought you thought of me as attractive, but that you didn’t actually like me as more than just some guy you had to put up with because your best friend is a werewolf,” Derek says, and when Stiles looks at him, the werewolf is smiling.

“You love me?” Stiles asks hopefully.

“I just said I did,” Derek shoots back playfully.

“So you knotted me because you love me?” Stiles asks.

“I knotted you, because I see you as someone who could be my mate,” Derek replies.

“Fuck yes,” Stiles says before lunging at Derek and kissing him deeply.

  
  


**Author's Note:**

> Thanks for reading! Comment and give kudos if you enjoyed!


End file.
